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Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Photo gallery for Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

A balcony with a glass table and chairs, overlooking a marina with boats and a river.
A brick house with a front porch, surrounded by lush greenery and flowering plants.
An outdoor seating area with a glass-top table, chairs, and a view of a marina with boats.
A brick house with a covered porch and a visible number '1570' on the front.
A beach with a calm sea, a sandy shore, and a distant sunset over a hilly landscape.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Family fun awaits
    Top-rated for families.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Chesapeake Bay

Popular amenities

  • Patio
  • Dog-friendly
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Onsite parking available

Explore the area

View map
St Leonard, MD
  • Place, Flag Harbor Marina
    ‪3 min walk‬
  • Place, Northern Chesapeake Bay
    ‪14 min walk‬
  • Place, Matoaka Beach
    ‪17 min walk‬

Rooms & beds

2 bedrooms (sleeps 5)

Convertible bed(s)

1 Double Futon

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Dining area

Add dates for prices

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About the area

St. Leonard

Located in St. Leonard, this cottage is near a water park and on the waterfront. Flag Harbor Marina and Perigeaux Vineyards and Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Chesapeake Bay and Battle Creek Cypress Swamp Sanctuary. R&J's PlayPark and Kocen Arts Center are also worth visiting. Kayaking, power boating and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking nearby.
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Map
St Leonard, MD

What's nearby

  • Flag Harbor Marina - 3 min walk - 0.3 km
  • Flag Ponds Nature Park - 12 min walk - 1.1 km
  • Northern Chesapeake Bay - 14 min walk - 1.2 km
  • Matoaka Beach - 17 min walk - 1.5 km
  • Maryland International Raceway - 53 min drive - 62.4 km

Getting around

  • Ronald Reagan National Airport (DCA) - 73 min drive

Restaurants

  • ‪Linda's Produce Stand - ‬9 min drive
  • ‪Frying Pan - ‬14 min drive
  • ‪Gateway Restaurant & Lounge - ‬12 min drive
  • ‪The Tavern - ‬5 min drive
  • ‪Patuxent Seafood Company - ‬17 min drive

Frequently asked questions

Is Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much does it cost to stay at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

As of 31 October 2026, prices found for a 1-night stay for 2 adults at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach on 1 March 2027 start from NZ$1,718, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

On-site parking is available at the property.

What time is check-in at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

Check-in begins at 3:00 PM.

What time is check-out at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

Checkout is at 11:00 AM.

Where is Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach located?

Situated on the waterfront, this cottage is steps away from Chesapeake Bay and Flag Harbor Marina. Long Beach and Northern Chesapeake Bay are also within 15 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 151 out of 176 reviews
Rating 8 - Good. 23 out of 176 reviews
Rating 6 - Okay. 1 out of 176 reviews
Rating 4 - Poor. 1 out of 176 reviews
Rating 2 - Terrible. 0 out of 176 reviews

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our 5th stay at this cottage. We return year after year because our accommodations are a perfect fit for our needs. The owners are wonderful. We look forward every year to returning.
Stayed 14 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
My family had a great stay at this cottage. Cottage was very clean and was well equipped for our stay. Centrally located to all the amenities in the area and we highly recommend. Host was very organized and communicated quickly when needed. We will be staying here in the future. Can’t wait to return.
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
.
Stayed 8 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Katherine was a pleasure to deal with. Communicating with her was easy and she responded very quickly. The house was as described and everything was neat, clean and organized. It was relaxing to sit on the deck and watch the boats coming and going across the street at the Marina. The beach was really nice and we went down and BBQed there. It is an easy walk, but we took the car to make it easier with all our stuff.I highly recommend checking this home out.
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent!
Stayed 4 nights in May 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Enjoyable stay, very quiet area, house was nice; water filters on kitchen sink and refrigerator would be nice. Tubs not elderly friendly and beds could be upgraded. Overall we really like the place.
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
My wife and me rented this cottage to be closer to our family while in the area. We were expecting busy days so we were looking for peaceful nights and that's exactly what we were given. I grew up in Owings and have family scattered throughout Southern Maryland so the location was perfect for visiting in the area plus making a couple of visits to Washington DC while we were in the area. My wife and I enjoyed coming back each night to the clanking of the sail boat rigging that came with the excellent view of the marina. We are definitely planning on returning to this quiet getaway on our next trip to Maryland.
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was easy to communicate with. The place is wonderful!
Stayed 21 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property we loved it

I will be back next year this location was great.
Stayed 5 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

My mother loved the harbor and beach that was right there.
Stayed 7 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great! The cottage was well appointed. The hosts were very welcoming, and the all the people we met on our walks were very friendly. I would definitely recommend this cottage.
Stayed 20 nights in Dec 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great hosts and great property. The location is nearly perfect. We might have been the first guests of the season or at least when bookings are light, so there were some bumps, but things happen and the hosts made sure everything was handled as best as possible. This might our new "spring break" place! We need to practice our fossil hunting skills because we are terrible!
Stayed 4 nights in Apr 2026
Response from VrboOwner on 15 April 2026
I’m glad we were able to solve your problems quickly and not interfere with your vacation.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Another great stay at Harbor Cottage. We stay there at least once a year and look forward to it every time. Can't beat the location, neighborhood or convenience to the private beach. The cottage is charming with a great view of Flag Harbor right across the street.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet Chesapeake Getaway

Cozy spot on bay. Great for beach hikes and birdwatching.
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was everything as advertised and more!! We loved it so much that we could live there forever!!Katherine was awesome!!!
Our pup Winnie exhausted from exploring all day in her bed for the night.
My husband Bob enjoying the bay with Winnie.
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely Home Near the Beach

House had everything we could have asked for, well stocked kitchen and lots of great information on local attractions available! Very nice location, great value!
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Get-Away

This was our 3rd summer visit to this home. We love it and will visit again!
Stayed 6 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect beachside retreat

This house was the perfect fit for our stay in st Leonard. The kitchen was well appointed and the facility was very comfortable. We would definitely stay here again.
Stayed 4 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love Staying at Harbor Cottage

Another great stay. The location and charm of Harbor Cottage can't be beat if you are going to the Calvert Cliffs area! Katherine is a wonderful host.
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
stay was excellent as always. great Neiborhood to enjoy beach with family and dogs. host was a pleasure to deal with. look forward to another season.
Stayed 15 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another Wonderful Stay at Harbor Cottage!

Had a great time. Many thanks to our hosts.
Stayed 4 nights in Apr 2023
Archival

10/10 Excellent

Perfect cozy cottage!!! We loved our stay!

Everything about our experience was perfect- from the reservation to check out. Katherine was very hospitable! The cottage was perfect for our family gathering- clean and comfy beds were also a plus 👍🏻Can’t wait until our next visit!!
Stayed 4 nights in Dec 2017
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We Our stay was perfect. The cottage was spotless and had everything we needed.The beach was a minute away and the view off the porch was great. We like to birdwatch and it was fantastic in the marina. We will definitely return.
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great little cottage!

We had a wonderful stay at harbor cottage! It was very clean and comfortable. The area is fantastic if you’re looking for someplace to chill and relax. Very dog friendly!
Stayed 4 nights in Apr 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Return trip, great location and property.

This is our second stay, and had a great time on the beach! The house is fully equipped with everything you need and is comfortable. We had a great time and will be back next year!
Stayed 4 nights in May 2023
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